Vacation Rentals & Apartments in Naples

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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

Match: DVD player Iron Staffed property Swing set or jungle gym Swimming pool

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Price per night from

$265

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

Match: DVD player Iron Staffed property Swing set or jungle gym Swimming pool

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Price per night from

$114

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$160

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: DVD player Iron Staffed property Swing set or jungle gym Swimming pool

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Price per night from

$742

Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$343

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

Match: DVD player Iron Staffed property Swing set or jungle gym Swimming pool

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Price per night from

$117

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Pink Gulfside Cottage, 100 steps to beach, Pet OK, Restored Beach House

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

4 of 5 match: Swimming pool, DVD player, Iron, Staffed property, Swing set or jungle gym

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Price per night from

$286

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: DVD player, Iron, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$620

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

4 of 5 match: DVD player, Iron, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$191

Responds fast! avg. 11 minutes

4 of 5 match: DVD player, Iron, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$132

2 Bedroom, 2 Bathroom condo / Heated pool / 7 minute walk to beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: DVD player, Iron, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$178

Southern Dunes Golf Vacation Villa

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Visitor” Loved it. Great neighborhood. Clean house. Easy to get a hold of people if you had questions or needed help. Walmart right around corner. Had everything you need to cook with. Great place. Defiantly will come back and recommend to anyone.

4 of 5 match: Iron, DVD player, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$117

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

4 of 5 match: Iron, DVD player, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$1,141

“Great cozy home away from home.” We stayed in the Orleans bungalo apartment on July 15-18. It felt like we were at home. The apartment had lots of character and charm. Loved sitting outside on the terrace watching the free entertainment across the street , was it called the ship wrecked bar? I especially loved beiing able to go to the back alley and washing clothes. (I hope it belonged to the cottages property, if not then oops!) We utilized the kitchen and the gas grill out back on the patio.Everything was great and this cottage had plenty of space for two families. We met my cousins from Texas in Flordia for a vaca. We drove from Oklahoma. The flat screens worked great. I have no complaints about this place. I just want to say to all you all snotty people leaving negative comments.... Quit complaining or find somewhere else to stay. What exactly do you think you are getting when you hear the word "cottages" it's not going to have a bell hop and a maid that cleans up your messes daily. Maybe some of you never lived in 100 year old homes and only used to a lavish lifestyle. Obviously you spent your time in doors. not us we were at the beach the majority of the day until almost 9pm every night. I enjoyed my stay there. It was a good 3 day stay for us despite the rainy weather. Yet we still had fun.

4 of 5 match: Swimming pool, DVD player, Iron, Staffed property, Swing set or jungle gym

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Price per night from

$296

Lemon Cottage, Pets OK , 200 Steps to Beach

Clearwater cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

4 of 5 match: Swimming pool, DVD player, Iron, Staffed property, Swing set or jungle gym

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Price per night from

$296

Steps from Beach, Pets OK, Sleeps 6, Clearwater Beach. 2 Bedrooms

Clearwater apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

4 of 5 match: Swimming pool, DVD player, Iron, Staffed property, Swing set or jungle gym

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Price per night from

$376

4 of 5 match: Swimming pool, DVD player, Iron, Staffed property, Swing set or jungle gym

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Price per night from

$423

January~April 2024

Estero apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Staffed property, DVD player, Iron, Swing set or jungle gym, Swimming pool

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Price per night from

$191

Make Memories at Paradise in Bella Terra - Amazing Vacation Condo!

Estero condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Staffed property, DVD player, Iron, Swing set or jungle gym, Swimming pool

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Price per night from

$149

BT61168 - Solterra Resort - 5 Bed 4.5 Baths Villa

Davenport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

4 of 5 match: Staffed property, DVD player, Iron, Swing set or jungle gym, Swimming pool

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Price per night from

$291

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

4 of 5 match: DVD player, Iron, Staffed property, Swing set or jungle gym, Swimming pool

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Price per night from

$172

REDUCED FOR APRIL!

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$170

Perfect View: 2-bedroom Unit at Prestigious Vasari

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$266

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$208

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$343

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$270

Island Escape

Goodland condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$286

Condo on the Key

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$206

Naples, Fla., First floor, 2BR 2BA. two blocks to

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 36 minutes

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$245

Falling Waters gated community in Naples Florida

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$229

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$143

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$283

Updated Indian Rocks Beach, Florida Beach Condo 1st Floor, Steps to Beach!

Indian Rocks Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Florida 2017 vacation” We stayed in room 107 at 50 Gulfside condo. It was a quite relaxing condition with everything we needed. I always appreciate comfortable beds and thick towels. We had that. There was a few nice restaurants walking distance away. There was also a nice coffee shop and a CVS close by. For $5.00 you could ride the bus from Clearwater to St Pete beach. We had our 20 year old granddaughter along and there wasn't much for her to do in the evening. We were there two weeks, and everything went well. The price per night was reasonable. The only downside is the bathrooms are very small.

Responds fast! avg. 3 hours 35 minutes

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$297

Luxury Beachfront Condo- Gulf Views From Every Room

Pelican Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$394

Luxurious Penthouse Oasis - Beachfront/Oceanfront

Redington Shores condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$685

SURF AND TURF ACTIVITY FILLED GOLF RESORT COMMUNITY

Venice villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 31 minutes

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$86

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$143

Zilli Ocean Front 202 & Suite

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

4 of 5 match: Swing set or jungle gym, DVD player, Iron, Staffed property, Swimming pool

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Price per night from

$307

Viewing 38 of 5,075
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